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The Second Chance Pell (SCP) program in 2015 enabled colleges and universities around the nation to offer Pell grants to incarcerated students since the ban in 1994. This instrumental case study seeks to fill a gap on the literature and provide further analysis of the application and implementation processes of administrators involved with their school’s SCP program using organizational policy conceptual framework. Three themes emerged from document analysis of the application letters and 15 semi-structured interviews: the college’s perspectives in intent, the organizational culture clash between the colleges and Department of Corrections, and the expectations versus realities experienced during the implementation process. These findings offer administrators suggestions for effective implementation of complicated, dual-bureaucracy programs and recommends avenues for further investigation.